Synlett, Inhaltsverzeichnis Synlett 2019; 30(07): 851-856DOI: 10.1055/s-0037-1611754 letter © Georg Thieme Verlag Stuttgart · New York Direct N-sec-Alkylation of Amides by Reaction of α-Halohydroxamates and Sulfonylindoles: An Approach to 3-Indolyl Methanamines Yuan Chen a College of Pharmacy and Biological Engineering, Chengdu University, Chengdu City 610106, P. R. of China b College of Chemistry and Chemical Engineering, China West Normal University, Nanchong City 637002, P. R. of China eMail: kangtairan@sina.com , Xiaoqiang Guo a College of Pharmacy and Biological Engineering, Chengdu University, Chengdu City 610106, P. R. of China , Chuang Zhou a College of Pharmacy and Biological Engineering, Chengdu University, Chengdu City 610106, P. R. of China , Lianmei Chen a College of Pharmacy and Biological Engineering, Chengdu University, Chengdu City 610106, P. R. of China , Tairan Kang * a College of Pharmacy and Biological Engineering, Chengdu University, Chengdu City 610106, P. R. of China b College of Chemistry and Chemical Engineering, China West Normal University, Nanchong City 637002, P. R. of China eMail: kangtairan@sina.com › Institutsangaben Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A catalyst-free, base-mediated N-sec-alkylation of amides by reaction of sulfonylindoles and α-halohydroxamates has been developed. The N-sec-alkylation of amides reaction is based on an intermolecular nucleophilic addition of vinylogous imine with N-(benzyloxy)meth-acrylamide/azaoxyallyl cations formed in situ and represents a simple way to give polyfunctionalized 3-indolyl methanamines in good to excellent yields. Key words Key words3-indolyl methanamines - azaoxyallyl cations - vinylogous imine - sulfonylindoles - α-halohydroxamates Volltext Referenzen References and Notes 1a Somei M, Yamada F. Nat. Prod. Rep. 2004; 21: 278 1b Faulkner DJ. Nat. Prod. Rep. 2002; 19: 1 1c Shirakawa S, Kobayashi S. Org. 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The crude product was purified by flash column chromatography on silica gel [flash column chromatography eluent, petroleum ether/ethyl acetate (6:1–4:1, v/v)] to give the pure product 3a (37 mg, 91% yield) as an oil. 1H NMR (400 MHz, CDCl3): δ = 7.37–7.34 (m, 3 H), 7.30–7.27 (m, 3 H), 7.23–7.21 (m, 1 H), 7.16–7.13 (m, 3 H), 7.11–7.08 (m, 1 H), 6.96–6.92 (m, 1 H), 6.77 (d, J = 6.94 Hz, 2 H), 5.48 (s, 1 H), 5.35 (s, 1 H), 4.95 (s, 1 H), 4.59 (d, J = 8.68 Hz, 1 H), 3.96 (d, J = 8.70 Hz, 1 H), 2.20 (s, 3 H), 2.06 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 171. 4, 141.1, 139.9, 135.1, 134.9, 134.4, 129.5, 129.3, 128.6, 128.5, 128.4, 128.3, 128.1, 127.0, 126.8, 121.3, 119.8, 119.7, 117.3, 110.3, 108.7, 78.6, 57.4, 20.4, 12.5. HRMS: m/z [M+H]+ calcd for C27H26N2O2: 410.2013; found: 410.2016. 15 CCDC 1546337 (3g) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data request/cif. Zusatzmaterial Zusatzmaterial Supporting Information CIF File
